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Discouraged from reaching out. How can I tell if my entrepreneur man is still interested?

Tagged as: Dating<< Previous question   Next question >>
Question - (16 June 2016) 3 Answers - (Newest, 20 June 2016)
A female United States age 30-35, anonymous writes:

I wanted to repost with better details. I’ve been dating a successful entrepreneur, early 30s, for about 2.5 months. He’s been traveling about half the time we’ve been together. During the first half of dating (traveling or not), he was very affectionate and chatty. During the first two weeks we hung out the two entire weekends (which I would normally find excessive but didn’t mind with him). We had a lot to talk about and could talk about anything, and there was a lot of attraction. He reached out to me daily and I sometimes did as well. When talking about what we’re looking for, and watching his actions as well, it seems we’re a great match.

About a month ago, he said he doesn’t play games (which I already knew) and usually doesn’t “chase” women because he doesn’t have time, but he really likes me. I’m the first woman he’s called (usually texts) and he also mentioned he doesn’t like small-talk through texting. He’s been single for 5 years but has dated. After this conversation he went on a business trip and his communication dropped like a hot potato. He reaches out every 1-3 days, asking how’s my day, but when I reach out he either responds immediately or can take up to 24 hours to respond. I miss the way he was before but I understand daily communication isn’t sustainable especially for someone as busy as he is.

I understand his business comes first. It’s his dream and I support him. I’m proud of him (even won an award recently) but I’m having trouble drawing the line between “busy” and “less interested.” He returned early last week from a business trip, and has another business trip this weekend. The week in between has been very busy with work piled up, and little communication between us. I actually thought we weren’t going to meet again, as I couldn’t tell if he was doing a slow fade away. But on Friday he asked me to dinner Sunday, which was our first meet in two weeks. The next morning I suggested dinner Tuesday. He agreed but cancelled the day of saying he’s very stressed, then changed his mind right away saying a quick dinner would be fine. I could tell he was mentally absent (even left a couple of items in the restaurant) and tired. So I told him to go home and get some rest. He needed alone time.

I don’t mind dating a busy man as long as he’s genuine to me, as I’m successful myself and have my own life. I do work standard hours though and have weekends free. His schedule is less predictable and the past couple times I’ve asked him out, he couldn’t go due to work (he does explain, for example telling me his client meeting schedule). He does ask me out though, and when I’m free I agree. However it discourages me from initiating as the ball is always in his court. I feel it’s not just dependent on his work schedule but his energy level as well. Sometimes I just want to tell him I’m thinking of him or proud of him through text, but I don’t because I’m afraid he’ll respond 24 hours later.

I don’t want to come off as clingy or annoying either. The last woman he dated (for 1-1.5 months according to him) asked him to call her daily. He said he broke it off because he knew in his heart he couldn’t keep it up. He’s usually the one who breaks up with the other (as I am too). I want to do my part… But should I just leave the ball in his court? Wait and see if he continues to reach out and ask me out? How can I tell if he’s busy or losing interest? Normally I wouldn’t bat an eye but he’s an amazing guy and worth the extra effort to me.

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A female reader, aunt honesty Ireland +, writes (20 June 2016):

aunt honesty agony auntAfter reading the couple of posts that you have had up recently I really don't think things are going to work out between you both. I can understand that he is a busy man, but it does not take long daily to make a phone call to keep in touch, believe me if he really wanted to keep in contact then he would have, nobody is busy 24 hours a day.

I think what he is looking for is a part time girlfriend, he may not play games, but he does not have time for a relationship, when he is free then he may want to hang out, but you are not a priority to him. The best advice I can give you is if you don't feel he is giving you enough attention then end it.

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A female reader, Marusela United Kingdom +, writes (18 June 2016):

Love,

I'm not surprised you are confused as I am too.

At the beginning of the relationship you were two very independent people without any intention of been tied up, You even said that you'd find two weekends together too much, even calling daily was excessive.

Now you have changed the expectations. You want him to be something he wasn't at the beginning. You want him to dote on you.

I don't think it's fair on him, or even on you.

You need to think why you want him to call you now. Is it because you are really attracted to him? Is it because now he's not interested you feel hurt and losing?

You need to have a clear idea of what you want first and, then, explain to him how you feel. If it's true neither of you play games, a honest conversation will make clear what you both want, where you are at, and how to move forward with your lives, together or apart.

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A female reader, Tisha-1 United States +, writes (17 June 2016):

Tisha-1 agony auntTranslation help from an old lady.

During the first half of dating (traveling or not), he was very affectionate

= he was trying to put his best foot forward

and chatty. During the first two weeks we hung out the two entire weekends (which I would normally find excessive but didn’t mind with him).

= he was doing an immersion study with you (I’m guessing he got you in bed?”

We had a lot to talk about and could talk about anything, and there was a lot of attraction.

= he was willing to talk and was trying actively to seduce you

He reached out to me daily and I sometimes did as well.

= he took a few seconds out of his day to send a random text

When talking about what we’re looking for, and watching his actions as well, it seems we’re a great match.

= did you actually reach the conclusion together that you were a great match? Obviously you discussed your goals and wishes but did he actrually say that you two were a great match?

i could keep going but I think it’s not worth my time, nor yours. He’s busy, fair enough. He’s not enough into you to chase you. Trust me, if he wanted to be with you, he’d be all over you....

He may well be an amazing entrepreneur but he’s crap at being a boyfriend. Don’t you deserve better?

I would leave the ball in his court and see what happens.

P.S. You can do better. While it’s great he’s so focussed on his career and is winning awards, yadda yadda yadda, he doesn’t sound like the boyfriend you want. If you were cool with his super casual and absent style he’d be the most amazing boyfriend ever... but you want a guy who wants to communicate with you daily. Not that big an ask.

He couldn’t call his last girlfriend daily? For me, that would be a big old PASS! NEXT! Buh bye, super entrepreneur, I deserve better.

But of course if you have bought into his amazing resume and can’t entertain the idea that there are better candidates for the boyfriend position, you will have to learn this the hard way.

Good luck! I do hope you realize you are worth a daily phone call. And more. Much much more.

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